The Montreal Canadiens won their league-leading 24th (and, to date, last) Stanley Cup against the Los Angeles Kings in 1993, during the 100th anniversary of the Stanley Cup. That playoff season, the Canadiens won an NHL-record 10 consecutive overtime games. They also tied an NHL-record by winning 11 consecutive games in one playoff year (the record is shared by the Pittsburgh Penguins and the Chicago Blackhawks - both teams won 11 in a row the previous year).
But in 1995, the Canadiens missed the playoffs for the first time in 25 years, and only the third time in 54 years. In December of that year, when the Canadiens lost 11-1 at home to the Detroit Red Wings, then-head coach Mario Tremblay refused to pull Patrick Roy from the net until after the ninth goal, despite the goalie's repeated pleas. After he was pulled, Roy, approached then team president Ronald Corey and told him, "This is my last game in a Montreal Canadiens uniform." He was traded to the eventual Stanley Cup Champion Colorado Avalanche along with Mike Keane for Jocelyn Thibault, Andrei Kovalenko, and Martin Rucinsky.
No team from Canada has won it since.On March 11, 1996, the Canadiens defeated the Dallas Stars, 4-1 in the final game at the historic Montreal Forum. The final goal at the Forum was scored by Andrei Kovalenko. The Stars were chosen as the final Forum opponent because their captain, Guy Carbonneau, and their general manager, Bob Gainey, were both former Canadien captains. Following the game, a moving closing ceremony was held, in which each living Canadiens captain, wearing an up-to-date version of the uniform with his old number on it, passed a torch, the older one to the younger one: Butch Bouchard to Maurice Richard to Jean Beliveau to Henri Richard to Yvan Cournoyer to Serge Savard to Gainey to Carbonneau to Pierre Turgeon, the then-captain. (Three living former captains were unavailable because they were still active with other teams: Mike Keane with the Avalanche, Kirk Muller with the New York Islanders, and Chris Chelios with the Chicago Blackhawks).
The team moved into the new Molson Centre (renamed Bell Centre for 2003-04) the following Saturday, defeating the New York Rangers, 4-2. However, the Canadiens missed the playoffs three straight seasons between 1999 and 2001. There was even brief talk of the team moving, especially after American investor George N. Gillett Jr. was the only interested buyer when the Molson family sold the team in 2001. After no acceptable offers came from Canadian interests, the NHL allowed Gillett to buy the team, provided that he promise to keep it in Montreal until 2021.
In the fall of 2001, it was revealed that centre Saku Koivu, who had been with the team since 1995, had cancer and would miss the season. However, he came back to win the Bill Masterton Memorial Trophy for perservance, sportsmanship and dedication to hockey, register two assists in the last three games and, along with the surprising strong play of goalie Jose Theodore (who won the Roger Crozier Saving Grace Award, Hart Trophy and Vezina Trophy that season), inspired the team for a run to the 2002 playoffs as the final seed in the Eastern Conference. They upset the Boston Bruins in the first round, before bowing to the Carolina Hurricanes in the second round.
On November 22, 2003, the Canadiens participated in the Heritage Classic, the first outdoor hockey game in the history of the NHL. The Canadiens defeated the Edmonton Oilers 4-3 in front of more than 55,000 fans — an NHL attendance record — at Commonwealth Stadium in Edmonton. The team seemed to turn a corner at that point, and finished the season in the 7th playoff seed in the Eastern Conference. The team would again play the Bruins in the playoffs, for a record 30th time. Coming back from a 3-1 deficit, the Canadiens won the final three games to again upset the Bruins. The Canadiens were swept away in second round by the eventual Stanley Cup champions Tampa Bay Lightning.
On January 13, 2006, Claude Julien was fired as coach, and replaced on an interim basis by Bob Gainey, the team's general manager. Later on in the season, Montreal starting goalie Jose Theodore was traded to the Colorado Avalanche after numerous disappointing starts, in return for goalie David Aebischer. The Canadiens narrowly made the playoffs, but lost in 6 games to the eventual champion Carolina Hurricanes.
In the 2006-07 NHL season, Guy Carbonneau took over as head coach of the team.
In December 2006, as the founder of the Montreal Canadiens, John Ambrose O'Brien was an inaugural inductee in the team's newly created 'Builders Row' in the Bell Centre. As well, the team inducted special advisor William Northey, former team president Donat Raymond and former owners Leo Dandurand, Joseph Cattarinich, Louis A. Letourneau and Senator Hartland de Montarville Molson.